Game of thrones: The men who would be Ballmer

Nobody knows why Microsoft’s Windows chief Steven Sinofsky unexpectedly jumped ship last Monday, despite rampant but unverifiable rumors. But Sinofsky is simply the latest in a long line of potential CEOs who’ve left Microsoft, as CEO Steve Ballmer’s controversial tenure continues with no heir apparent in sight — and perhaps not desired. Still, those who’ve left Microsoft could be named Ballmer’s successor at some point.

Back in July 2009, Ballmer reorganized Microsoft and named five presidents: Sinofsky was president of the Windows and Windows Live division, Bob Muglia was president of Server and Tools, Qi Lu was president of Online Services, Stephen Elop was president of the Business division, and Robbie Bach was president of the Entertainment and Devices division. Three years later, they’re all gone, except for Lu.

Perhaps it’s true, as some have alleged, that Ballmer intends to run Microsoft forever. Or maybe the conspiracy theorists are right in saying that Sinofsky’s departure is part of a diabolical master plan that will bring him back, Steve Jobs-like, when Microsoft needs him most. But looking around at the current landscape, it’s awfully hard to see any successor for Ballmer, either inside or outside the company.

Maybe that’s the way he wants it.

Here are the best-known former Microsoft executives who have left in the past four years, and my estimates of who could still run Microsoft as CEO one day:

Jeff Raikes (left in 2008): He has broad experience with Microsoft and the Microsoft way. A Stanford University grad, he spent 27 years with Microsoft, was recruited by Ballmer in 1981, had strong experience in designing the Office programs, was promoted to VP of Office, then retired as president of the Information Worker business line. He left Microsoft to become CEO of the Bill & Melinda Gates Foundation, a position he holds today.

Raikes is part-owner of the Seattle Mariners baseball team and the founding donor for the University of Nebraska’s School of Computer Science and Management. Of all the former Microsoft execs who maybe potential Ballmer replacements, he’s at or near the top of the list.

J Allard (left in 2010): He has wide experience with many parts of Microsoft, but he’s best known for his work on the Xbox, Zune, the ill-fated Kin, and the underappreciated Courier two-screen tablet, which might have out-Appled the iPad had it ever come to light. Many people both inside and outside Microsoft remember his groundbreaking white paper “Windows: The Next Killer Application on the Internet,” released in 1994, that helped get Microsoft turned toward the cloud.

Allard left Microsoft shortly after he lost a shoot-out with Sinofsky: Allard wanted to push ahead with the two-screen Courier tablet that complemented, rather than replaced, the PC. While Windows focused on getting the job done, Courier was meant to be light on traditional applications, such as email, and instead aimed at creative souls who wanted to sketch, sort photos, or block out a novel. Ballmer finally decided, with Bill Gates’ input, to side with Sinofsky, kill the Courier, and go ahead with the new tablet-friendly but still PC-focused Windows 8.

Allard’s departing memo, reprinted by Time, remains a classic motivator. But Allard as a CEO? It’s hard to envision a free spirit like Allard at the helm of a company that makes most of its money from servers and Office.

Robbie Bach (left in 2010): He and Allard formed quite a team, with Allard covering the engineering side and Bach on the business side. Bach rapidly rose in Microsoft to head the business side of Microsoft Office in the 1990s. When Bach left in May 2010, he was the president of the Entertainment & Devices division, which included Xbox, Zune, Windows Mobile, Microsoft TV, Kin, and Courier. He, too, left Microsoft when Ballmer killed Courier. Bach’s now primarily involved in philanthropic pursuits, particularly the Boys & Girls Club of America.

Stephen Elop (left in 2010): He didn’t so much leave Microsoft as rescued a foundering customer, Nokia. He’s currently CEO of Nokia, the ill-fated former mobile phone superstar that, under Elop’s leadership, has bet its existence on Windows Phone. Opinions vary on Nokia’s long-term viability, particularly if Microsoft proceeds with its rumored Microsoft-branded smartphone.

Elop doesn’t have much experience with Microsoft. He was COO of Juniper Networks before joining Microsoft in January 2008, and he left for Nokia in September 2010. You could argue he’s currently gaining experience with Microsoft, even if from a different perspective, but few believe he’s in line to take over for Ballmer.

Ray Ozzie (let in 2010): He retains his mythical standing among many Microsoft observers. Handpicked by Gates to oversee Microsoft’s software design efforts, Ozzie departed quickly, for reasons still unknown. But as I described at the time, he had plenty of reason to leave: very slow progress with cloud computing, Ozzie’s forte; a stunning dumbing-down of his vision of Azure cloud services; the stunting of Live Mesh, rolled into a like-named but quite different Windows Live product; and cancellation of the Live Labs effort.

I see the hand of Sinofsky in most of those anti-Ozzie developments. And Business Insider has published remarks from an unidentified “former Microsoft executive who spent years working with Sinofsky” saying, “Ozzie produced some products that you could think of as cloud-based fabric products. The plan was that Ozzie would hand them over to Sinofsky’s team and Sinofsky’s team would ship them. [But] when those products made it into Sinofsky’s team, Sinofsky effectively killed them…. There’d be no discussion about it. He’d just kind of passively aggressively do it. Take the product and kill it.”

Let us not forget Ozzie’s upstaging of Ballmer at the D8 Conference in June 2010. If you watch the interview, you can’t help but be impressed at how well Ozzie understands the cloud — in very stark contrast to Ballmer.

Would Ozzie come back to take over from Ballmer? When pigs fly is my guess. Still, I was very surprised to discover that Ozzie owns almost as much Microsoft stock as Sinofsky.

Bob Muglia (left in 2011): He was one of the most respected techies in Microsoft, from my experience, anyway, when Muglia left as president of the Server and Tools Division last year. A server person since day one, Muglia turned Server and Tools into an unparalleled money machine, but some complained that his extensive experience with corporate server installations wouldn’t prepare him for competition in a cloudy world. Others noted that Muglia and Sinofsky were infamously incompatible.

Andy Lees (sidelined in 2011): Ballmer shocked the mobile community when he all but fired Windows Phone division president Lees in December 2011. More accurately, Lees was transferred to a position with a vague responsibility, reporting directly to Ballmer. But Lees jumped back into the limelight in May 2012, when we learned that Lees had brokered an agreement between Microsoft and Barnes & Noble that led to Microsoft investing $300 million in a Nook tablet joint venture.

Quietly, in early October 2012, Lees was turned into a corporate vice president at Microsoft, working on “corporate development and strategy” for CFO Peter Klein. Few people knew about the move until late last week, when Dina Bass at Bloomberg posted the details.

It strikes me that Lees may have been put on the sidelines while Sinofsky, um, influenced the development of Windows Phone 8. Now that Sinofsky’s gone, the coast is clear for Lees to get back the keys to the executive washroom. Notably, Lees didn’t lose his title of president even while sidelined.

Paul Maritz (left in 2000): He spent 14 years at Microsoft, managing Windows 95, Windows NT, and Internet Explorer, among many other products, with a heavy technical background. His departure coincided with the release of Windows Millennium. Until he left, many people considered him to be the most senior executive at Microsoft, behind Gates and Ballmer.

Maritz’s departure came around the same time as many other Microsoft legends — Jim Allchin, Nathan Myhrvold, Greg Maffei, Pete Higgins, and Brad Silverberg all come to mind — but unlike the others, Maritz went on to lead a fierce and highly successful Microsoft competitor, VMware. In September, Maritz left as head honcho for what had become EMC’s VMware division and went to work for its parent company, EMC.

Is Maritz a possible Ballmer replacement? It’s certainly conceivable.